Alcohol with floral odor

ABSTRACT

The present invention relates to compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof and wherein one R represents a methyl group and the other R is a hydrogen atom; which are useful as perfuming ingredients.

This application is a 371 filing of International Patent ApplicationPCT/EP2014/072217 filed 16 Oct. 2014, which claims the benefit ofEuropean patent application n° 13192085.2 filed 8 Nov. 2013.

TECHNICAL FIELD

The present invention relates to the field of perfumery. Moreparticularly, it concerns the use as perfuming ingredient of compoundsof formula (I) as defined below, which are useful perfuming ingredientsof the lily of the valley/gardenia type. Therefore, following what ismentioned herein, the present invention comprises the invention'scompounds as part of a perfuming composition or of a perfuming consumerproduct.

PRIOR ART

To the best of our knowledge, 3-methyl-5-phenylhexan-1-ol was neverdisclosed and 4-methyl-6-phenylhexan-2-ol is mentioned only in onedocument. In said document, Helv. Chim. Acta 1979, 62 (7), 2361-2373,the compound of formula (I) is synthesized by reduction using Cobalt.However, this prior art document does not report or suggest anyorganoleptic properties of the compounds of formula (I), or any use ofsaid compounds in the field of perfumery.

To the best of our knowledge, the closest analogue known in theperfumery is the chemical 3-methyl-5-phenylpentanol also known asphenyhexanol and reported in the book by S. Arctander as n° 2200(Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA). We may alsocite 6-phenylheptan-2-ol reported in the book by S. Arctander n° 2575(Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA),2-methyl-5-phenylpentan-1-ol (known as Rosaphen®; origin Symrise AG,Germany) and 4-methyl-6-phenylheptan-2-ol described in Justus LiebigsAnn. Chem. 1962, 654, 131-145. However, among the known derivatives of5-phenylpentanol, the ones with a primary alcohol and one methyl groupas 3-methyl-5-phenylpentanol or as Rosaphen® are reported as having arosy note; and the ones with a secondary alcohol and two or three methylgroups as 6-phenylheptan-2-ol or 4-methyl-6-phenylheptan-2-ol show arosy or rhubarb note type. In other words, quite different notes arereported for the prior art compare with the present invention'scompounds.

These prior art documents do not report or suggest any organolepticproperties of the compounds of formula (I) and do not report or suggestany use of said compounds in the field of perfumery.

DESCRIPTION OF THE INVENTION

We have now surprisingly discovered that a compound of formula

-   -   in the form of any one of its stereoisomers or a mixture thereof        and wherein one R represents a methyl group and the other R is a        hydrogen atom;        can be used as perfuming ingredient, for instance to impart odor        notes of the lily of the valley/gardenia.

For the sake of clarity, by the expression “any one of itsstereoisomers”, or the similar, it is meant the normal meaningunderstood by a person skilled in the art, i.e. that the invention'scompound can be a pure enantiomer or diastereoisomer. Indeed, thecompounds of formula (I) have two stereogenic centers which can havedifferent stereochemistry (i.e. compound (I) can have (R,R) or (R,S)configuration). Each of said stereogenic centers can be in a relativeconfiguration R or S or a mixture thereof or in other words saidcompound of formula (I) can be in a form of pure enantiomer ordistereoisomer, or in a form of a mixture of stereoisomers.

As preferred examples of the invention's compounds, one may cite,4-methyl-6-phenylhexan-2-ol, which possesses an odor characterized by alily of the valley/gardenia and green notes with honey aspect. Thiscompound is very powerful in application and the floral note of thisingredient is significantly more substantive than the known compoundswith the same kind of floral note, such as styrallyl acetate. Itsorganoleptic character differentiates from the phenylhexanol by havinggreen connotation without rosy note and by its power. According to aparticular embodiment of the invention, compound of formula (I) is inthe form of a mixture of stereoisomers containing at least 80% of bothstereoisomers (2RS,4RS)-4-methyl-6-phenylhexan-2-ol and(2SR,4RS)-4-methyl-6-phenylhexan-2-ol. Preferably compound of formula(I) is in the form of a mixture of stereoisomers containing at least 50%of (2RS,4RS)-4-methyl-6-phenylhexan-2-ol. For the sake of clarity, bythe expression “2RS,4RS” it is meant an equimolar mixture of 2R,4R and2S,4S and by the expression “2SR,4RS” it is meant an equimolar mixtureof 2S,4R and 2R,4S.

As other example, one may cite 3-methyl-5-phenylhexan-1-ol, whichpossesses an odor similar to the one mentioned above but distinguishingitself by having a stronger gardenia/styrallyle note as well as a bitweaker green note and less clear.

TABLE 1 Invention's compounds and its odor properties and prior artcompounds Odor notes Compound structure and name

Lily of the valley/ gardenia and green notes with honey aspect No rosynote rac-4-methyl-6-phenylhexan-2-ol

Lily of the valley/gardenia No rosy note rac-3-methyl-5-phenylhexan-1-olPrior art compounds

Rosy note 3-methyl-5-phenylpentanol

Rose-blossom note and with somewhat geraniol

Oily-rosy and delicately green note 6-phenylheptan-2-ol

Rhubarb note slightly floral No gardenia note4-methyl-6-phenylheptan-2-ol

When the odor of the invention's compounds is compared with that of theprior art compounds, then the invention's compounds distinguishthemselves by a clearly gardenia/lily of the valley note and by lackingthe rosy note characteristic of phenylhexanol or 6-phenylheptan-2-ol.Furthermore, the rhubarb note reported for 4-methyl-6-phenylheptan-2-olis weaker for the invention's compound. Said differences lend theinvention's compounds and the prior art compounds to be each suitablefor different uses, i.e. to impart different organoleptic impressions.

As mentioned above, the invention concerns the use of a compound offormula (I) as perfuming ingredient. In other words, it concerns amethod to confer, enhance, improve or modify the odor properties of aperfuming composition or of a perfumed article, which method comprisesadding to said composition or article an effective amount of at least acompound of formula (I). By “use of a compound of formula (I)” it has tobe understood here also the use of any composition containing a compound(I) and which can be advantageously employed in perfumery industry.

Said compositions, which in fact can be advantageously employed asperfuming ingredients, are also an object of the present invention.

Therefore, another object of the present invention is a perfumingcomposition comprising:

-   i) as perfuming ingredient, at least one invention's compound as    defined above;-   ii) at least one ingredient selected from the group consisting of a    perfumery carrier and a perfumery base; and-   iii) optionally at least one perfumery adjuvant.

By “perfumery carrier” we mean here a material which is practicallyneutral from a perfumery point of view, i.e. that does not significantlyalter the organoleptic properties of perfuming ingredients. Said carriermay be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifyingsystem, i.e. a solvent and a surfactant system, or a solvent commonlyused in perfumery. A detailed description of the nature and type ofsolvents commonly used in perfumery cannot be exhaustive. However, onecan cite as non-limiting examples solvents such as dipropyleneglycol,diethyl phthalate, isopropyl myristate, benzyl benzoate,2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the mostcommonly used. For the compositions which comprise both a perfumerycarrier and a perfumery base, other suitable perfumery carriers thanthose previously specified, can be also ethanol, water/ethanol mixtures,limonene or other terpenes, isoparaffins such as those known under thetrademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycolether esters such as those known under the trademark Dowanol® (origin:Dow Chemical Company).

As solid carriers one may cite, as non-limiting examples, absorbing gumsor polymers, or yet encapsulating materials. Examples of such materialsmay comprise wall-forming and plasticizing materials, such as mono, di-or trisaccharides, natural or modified starches, hydrocolloids,cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteinsor pectins, or yet the materials cited in reference texts such as H.Scherz, Hydrokolloide: Stabilisatoren, Dickungs- and Geliermittel inLebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie,Lebensmittelqualität, Behr's Verlag GmbH & Co., Hamburg, 1996. Theencapsulation is a well known process to a person skilled in the art,and may be performed, for instance, using techniques such asspray-drying, agglomeration or yet extrusion; or consists of a coatingencapsulation, including coacervation and complex coacervationtechnique.

By “perfumery base” we mean here a composition comprising at least oneperfuming co-ingredient.

Said perfuming co-ingredient is not of formula (I). Moreover, by“perfuming co-ingredient” it is meant here a compound, which is used ina perfuming preparation or a composition to impart a hedonic effect. Inother words such a co-ingredient, to be considered as being a perfumingone, must be recognized by a person skilled in the art as being able toimpart or modify in a positive or pleasant way the odor of acomposition, and not just as having an odor.

The nature and type of the perfuming co-ingredients present in the basedo not warrant a more detailed description here, which in any case wouldnot be exhaustive, the skilled person being able to select them on thebasis of his general knowledge and according to intended use orapplication and the desired organoleptic effect. In general terms, theseperfuming co-ingredients belong to chemical classes as varied asalcohols, lactones, aldehydes, ketones, esters, ethers, acetates,nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compoundsand essential oils, and said perfuming co-ingredients can be of naturalor synthetic origin. Many of these co-ingredients are in any case listedin reference texts such as the book by S. Arctander, Perfume and FlavorChemicals, 1969, Montclair, N.J., USA, or its more recent versions, orin other works of a similar nature, as well as in the abundant patentliterature in the field of perfumery. It is also understood that saidco-ingredients may also be compounds known to release in a controlledmanner various types of perfuming compounds.

By “perfumery adjuvant” we mean here an ingredient capable of impartingadditional added benefit such as a color, a particular light resistance,chemical stability, etc. A detailed description of the nature and typeof adjuvant commonly used in perfuming bases cannot be exhaustive, butit has to be mentioned that said ingredients are well known to a personskilled in the art.

An invention's composition consisting of at least one compound offormula (I) and at least one perfumery carrier represents a particularembodiment of the invention as well as a perfuming compositioncomprising at least one compound of formula (I), at least one perfumerycarrier, at least one perfumery base, and optionally at least oneperfumery adjuvant.

It is useful to mention here that the possibility to have, in thecompositions mentioned above, more than one compound of formula (I) isimportant as it enables the perfumer to prepare accords, perfumes,possessing the odor tonality of various compounds of the invention,creating thus new tools for his work.

For the sake of clarity, it is also understood that any mixtureresulting directly from a chemical synthesis, e.g. a reaction mediumwithout an adequate purification, in which the compound of the inventionwould be involved as a starting, intermediate or end-product could notbe considered as a perfuming composition according to the invention asfar as said mixture does not provide the inventive compound in asuitable form for perfumery. Thus, unpurified reaction mixtures aregenerally excluded from the present invention unless otherwisespecified.

Furthermore, the invention's compound can also be advantageously used inall the fields of modern perfumery, i.e. fine or functional perfumery,to positively impart or modify the odor of a consumer product into whichsaid compound (I) is added. Consequently, another object of the presentinvention is represented by a perfuming consumer product comprising, asperfuming ingredient, at least one compound of formula (I), as definedabove.

The invention's compound can be added as such or as part of aninvention's perfuming composition.

For the sake of clarity, it has to be mentioned that, by “perfumingconsumer product” it is meant a consumer product which is expected todeliver at least a pleasant perfuming effect to the surface to which itis applied (e.g. skin, hair, textile, or home surface). In other words,a perfuming consumer product according to the invention is a perfumedconsumer product which comprises the functional formulation, as well asoptionally additional benefit agents, corresponding to the desiredconsumer product, e.g. a detergent or an air freshener, and an olfactiveeffective amount of at least one invention's compound. For the sake ofclarity, said perfuming consumer product is a non-edible product.

The nature and type of the constituents of the perfumery consumerproduct do not warrant a more detailed description here, which in anycase would not be exhaustive, the skilled person being able to selectthem on the basis of his general knowledge and according to the natureand the desired effect of said product.

Non-limiting examples of suitable perfumery consumer product can be aperfume, such as a fine perfume, a cologne or an after-shave lotion; afabric care product, such as a liquid or solid detergent, a fabricsoftener, a fabric refresher, an ironing water, a paper, or a bleach; abody-care product, such as a hair care product (e.g. a shampoo, acoloring preparation or a hair spray), a cosmetic preparation (e.g. avanishing cream or a deodorant or antiperspirant), or a skin-careproduct (e.g. a perfumed soap, shower or bath mousse, oil or gel, or ahygiene product); an air care product, such as an air freshener or a“ready to use” powdered air freshener; or a home care product, such as awipe, a dish detergent or hard-surface detergent.

Some of the above-mentioned consumer products may represent anaggressive medium for the invention's compound, so that it may benecessary to protect the latter from premature decomposition, forexample by encapsulation or by chemically bounding it to anotherchemical which is suitable to release the invention's ingredient upon asuitable external stimulus, such as an enzyme, light, heat or a changeof pH.

The proportions in which the compounds according to the invention can beincorporated into the various aforementioned articles or compositionsvary within a wide range of values. These values are dependent on thenature of the article to be perfumed and on the desired organolepticeffect as well as the nature of the co-ingredients in a given base whenthe compounds according to the invention are mixed with perfumingco-ingredients, solvents or additives commonly used in the art.

For example, in the case of perfuming compositions, typicalconcentrations are in the order of 0.001% to 10% by weight, or evenmore, of the compounds of the invention based on the weight of thecomposition into which they are incorporated. Concentrations lower thanthese, such as in the order of 0.01% to 5% by weight, can be used whenthese compounds are incorporated into perfumed articles, percentagebeing relative to the weight of the article.

The invention's compounds can be prepared according to a method reportedin the literature or standard methods known in the art as describedherein below.

EXAMPLES

The invention will now be described in further details by way of thefollowing examples, wherein the abbreviations have the usual meaning inthe art, the temperatures are indicated in degrees centigrade (° C.);the NMR spectral data were recorded in CDCl₃ (if not stated otherwise)with a 360 or 400 MHz machine for ¹H and ¹³C, the chemical shifts δ areindicated in ppm with respect to TMS as standard, the coupling constantsJ are expressed in Hz.

Example 1

Synthesis of Compounds of Formula (I)

a) 4-methyl-6-phenylhexan-2-ol

i) To 98 mL of heptane was added benzaldehyde (100 g, 0.94 mol),camphorsulfonic acid (0.26 g, 0.001 mol) dissolved in 0.3 g of water.The mixture was heated to a pot temperature of 98-100° C. Remove anywater in the flask as a water/heptane azeotrope (78° C. boiling point).When the flask temperature has stabilized, begin the addition ofmethylisoprenol (73.6 g, 0.74 mol). Approximately 13.2 g of water willbe removed azeotropically during the reaction. Let the reaction continueuntil water removal has stopped. This will be indicated by a 20° C. risein the vapor temperature at the top of the column slowly add 0.4 gsodium carbonate dissolved in 8 g of water to the flask. Check to makesure the pH is above 9. The two layers were separated and the aqueousphase extracted with 100 ml of ether. The two ethereal phases werecombined, washed with 50 ml of water and 50 ml of brine and dried overNa₂SO₄. Filtration and concentration gave 161 g of oil. This oil waspurified by vacuum distillation (68 to 100° C., 0.5 to 0.05 mbar)through a short path to give 100.5 g (61%) of a mixture of double bondisomers of 2-methyl-4-methylene-6-phenyltetrahydro-2H-pyran.

¹H NMR (400 MHz, CDCl₃): 7.40-7.36 (m, 2H), 7.35-7.30 (m, 2H), 7.27-7.22(m, 1H), 4.78 (m, 2H), 4.32 (dd, J=2.3 Hz, 0.5 Hz, 1H), 3.58 (m, 1H),2.42 (dt, J=2.7 Hz, 0.4 Hz, 1H), 2.24 (m, 2H), 2.03 (m, 1H), 1.30 (d,J=1.2 Hz, 3H).

¹³C NMR (100 MHz, CDCl₃): 22.0 (q), 42.3 (t), 42.7 (t), 74.9 (d), 80.4(d), 108.6 (t), 125.9 (d), 127.5 (d), 128.4 (d), 142.6 (s), 144.8 (s).

ii) To the mixture obtained in previous step (15 g, 0.079 mol) in theautoclave was added Pd/C 5% (ESCAT 11, 50% wet). Pressurize to 13 barwith H₂ and begin heating to 120° C. After hydrogenation of the olefin,the autoclave was vented off. pTsOH.H₂O (0.021 g, 0.001 mol) in 0.5 mlof water was added. After the p-toluenesulfonic acid has been added,pressurize back to 13 bar with H₂, raise the set point temperature to140° C., and continue the hydrogenation reaction for another 3 hours.Analyze by G.C. When the hydrogenation is complete, cool the autoclaveto RT and then vent to atmospheric pressure. Pressure the autoclave with2.5 bar of N₂ and vent again to atmospheric pressure to purge residualH₂. Repeat this purge and vent again. The mixture was filtered overCelite®, washed with 50 ml of saturated NaHCO₃ solution, washed with 50ml of brine. The organic phase was dried over Na₂SO₄. Filtration andconcentration gave 13.5 g of oil. This oil was purified by vacuumdistillation (100 to 150° C., 0.5 to 0.02 mbar) through a short path togive 13.2 g (87%) of 4-methyl-6-phenylhexan-2-ol as a mixture ofdiastereoisomers with the ratio 94/6 ((2RS,4RS)/(2SR,4RS)).

(2RS,4RS)-4-methyl-6-phenylhexan-2-ol

¹H NMR (400 MHz, CDCl₃): 7.33-7.22 (m, 2H), 7.22-7.12 (m, 3H), 4.02-3.83(m, 1H), 2.71-2.63 (m, 1H), 2.62-2.54 (m, 1H), 1.75-1.44 (m, 4H),1.41-1.32 (m, 1H), 1.25-1.20 (m, 1H), 1.18 (d, JHH=4.9 Hz, 3H), 0.97 (d,JHH=5.2 Hz, 3H).

¹³C NMR (100 MHz, CDCl₃): 142.9 (s), 128.3 (d), 125.6 (d), 65.7 (d),46.7 (d), 39.5 (t), 33.3 (t), 29.2 (t), 24.3 (q), 19.3 (q).

(2SR,4RS)-4-methyl-6-phenylhexan-2-ol

¹H NMR (400 MHz, CDCl₃): 7.30-7.24 (m, 2H), 7.21-7.15 (m, 3H), 3.96-3.84(m, 1H), 2.73-2.63 (m, 1H), 2.62-2.52 (m, 1H), 1.75-1.66 (m, 1H),1.65-1.57 (m, 1H), 1.49-1.36 (m, 3H), 1.29-1.20 (m, 1H), 1.16 (d,JHH=4.1 Hz, 3H), 0.98 (d, JHH=4.4 Hz, 3H).

¹³C NMR (100 MHz, CDCl₃): 142.9 (s), 128.3 (d), 125.7 (d), 66.2 (d),46.8 (t), 38.8 (t), 33.3 (t), 29.6 (d), 23.8 (q), 20.1 (q).

b) 3-methyl-5-phenylhexan-1-ol

i) A mixture of toluene (500 ml), acetophenone (120 g, 1 mole),isoprenol (129 g, 1.5 mol) and para-toluene sulfonic acid (3 g, 0.02mol) was heated under reflux 4 h until complete removal of water. Thereaction mixture was cooled to RT and filtered over Al₂O₃. Volatileswere evaporated and the crude mixture was purified by chromatography(hexane/ethyl acetate 9/1) following by distillation afforded 102 g of amixture of double bond isomers of2-methyl-2-phenyl-4-methylene-tetrahydropyrane (54%).

ii) To compounds obtained in previous step (10 g, 0.053 mol) in theautoclave was added Pd/C 5% (500 mg). Pressurize to 13 bar with H₂ andbegin heating to 120° C. After hydrogenation of the olefin, theautoclave was vented off. HCl (2 ml) was added. After the HCl has beenadded, pressurize back to 13 bar with H₂, raise the set pointtemperature to 140° C., and continue the hydrogenation reaction foranother 3 hours. Analyze by G.C. When the hydrogenation is complete,cool the autoclave to RT and then vent to atmospheric pressure. Pressurethe autoclave with 2.5 bar of N₂ and vent again to atmospheric pressureto purge residual H₂. Repeat this purge and vent again. The mixture wasfiltered over Celite®, washed with 50 ml of saturated NaHCO₃ solution,washed with 50 ml of brine. The organic phase was dried over Na₂SO₄.Filtration and concentration gave an oil which was purified bychromatography and distillation to give 4.7 g (46%) of3-methyl-5-phenylhexan-1-ol.

¹³C NMR (100 MHz, CDCl₃): 21.3, 21.4, 26.3, 36.3, 40.1, 43.4, 60.3,125.9, 128.1, 128.5, 147.7.

Example 2

Preparation of a Perfuming Composition

A perfuming composition for detergent was prepared by admixing thefollowing ingredients:

Parts by weight Ingredient 400 Isobornyl Acetate 200 Benzyl Acetate 100Phenylethyl Acetate 800 Verdyl Acetate 20 2-methylundecanal 50Cetalox ®¹⁾ 400 Citronellol 20 Coumarine 40 Allyl Cyclohexylpropionate150 (1′R,E)-2-ethyl-4-(2′,2′,3′-trimethyl-3′-cyclopenten-1′-yl)-2-buten-1-ol 800 Dihydromyrcenol 300 Eugenol 300(+−)-(1-Ethoxyethoxy)cyclododecane 200 Gamma Undecalactone 300 Geraniol60 500 Habanolide ®²⁾ 20 Hivernal ® Neo³⁾ 1000 Iso E ® Super⁴⁾ 40Isoeugenol Extra 1000 Isoraldeine 70 P 280 Linalool 100 Crystal moss 400Hedione ®⁵⁾ 40 Nirvanol ®⁶⁾ 20 Oxyde de Rose 400 Verdyl Propionate 600Benzyl Salicylate 40 Cis-3-Hexenol Salicylate 400 Salicynile ®⁷⁾ 100Orange Oil 150 Undecavertol ®⁸⁾ 800 Verdox ®⁹⁾ 30 10%* Violettyne 10000*in isopropyle myristate¹⁾dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan; origin:Firmenich SA, Geneva, Switzerland ²⁾pentadecenolide; origin: FirmenichSA, Geneva, Switzerland ³⁾3-(3,3/1,1-dimethyl-5-indanyl)propanal;origin: Firmenich SA, Geneva, Switzerland⁴⁾1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; origin:International Flavors & Fragrances, USA ⁵⁾methyl dihydrojasmonate;origin: Firmenich SA, Geneva, Switzerland⁶⁾3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol;origin: Firmenich SA, Geneva, Switzerland ⁷⁾(2Z)-2-Pnenyl-2-hexenitrile;origin: Firmenich SA, Geneva, Switzerland ⁸⁾4-methyl-3-decen-5-ol;origin: Givaudan SA, Vernier, Switzerland ⁹⁾2-tert-butyl-1-cyclohexylacetate; origin: International Flavors & Fragrances, USA

The addition of 500 parts by weight of 4-methyl-6-phenylhexan-2-ol tothe above-described composition imparted to the latter an overallconnotation in the direction of gardenia/lily of the valley. Theaddition of the same amount of the prior art phenylhenanol providedtotally different results which is clearly a rosy note.

Example 3

Preparation of a Perfuming Composition

A perfuming composition for air freshener was prepared by admixing thefollowing ingredients:

Parts by weight Ingredient 40 Hexyl Acetate 20 Isoeugenyl Acetate 50Aladinate ®¹⁾ 1000 Hexylcinnamic Aldehyde 400 Bergamote oil 10 EthylCaproate 50 Cetalox ®²⁾ 50 Raspberry ketone 40 Cis Jasmone 20Cis-3-Hexenol 300 Coranol ™³⁾ 10 Cyclogalbanate⁴⁾ 400(1′R,E)-2-ethyl-4-(2′,2′,3′-trimethyl-3′-cyclopenten-1′-yl)-2-buten-1-ol 20 Delta Damascone 500 Dihydromyrcenol140 Floralozone ®⁵⁾ 80 Gamma Undecalactone 1300 Habanolide ®⁶⁾ 1700Hedione ®⁷⁾ 40 Heliopropanal⁸⁾ 20 Heliotropine⁹⁾ 200 Ionone Beta 750 IsoE ® Super¹⁰⁾ 450 Phenoxy Isobutyrate 20 Isoeugenol Extra 500Isoraldeine ®¹¹⁾ 100 Lyral ®¹²⁾ 50 10%* 2,6-dimethyl-5-heptanal 40Methylbutyrate 2 Ethyle 100 Muscenone Delta¹³⁾ 100 Polysantol ®¹⁴⁾ 400Salicynile ®¹⁵⁾ 20 Triplal ®¹⁶⁾ 300 Undecavertol ®¹⁷⁾ 80 10%* Vanilline9300 *in dipropyleneglycol ** in isopropyle myristate¹⁾3-methyl-2-hexenyl acetate; origin: Firmenich SA, Geneva, Switzerland²⁾dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan; origin:Firmenich SA, Geneva, Switzerland ³⁾4-cyclohexyl-2-methyl-2-butanol;origin: Firmenich SA, Geneva, Switzerland ⁴⁾(cyclohexyloxy)-acetated'allyle; origin: Symrise, Holzminden, Allemagne⁵⁾3-(4/2-ethylphenyl)-2,2-dimethylpropanal; origin: InternationalFlavors & Fragrances, USA ⁶⁾pentadecenolide; origin: Firmenich SA,Geneva, Switzerland ⁷⁾methyl dihydrojasmonate; origin: Firmenich SA,Geneva, Switzerland ⁸⁾3-(1,3-benzodioxol-5-yl)-2-methylpropanal; origin:Firmenich SA, Geneva, Switzerland ⁹⁾1,3-benzodioxole-5-carbaldehyde;origin: Firmenich SA, Geneva, Switzerland¹⁰⁾1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; origin:International Flavors & Fragrances, USA¹¹⁾3-methyl-4-(2,6,6-trimethyl-2cyclohexen-1-yl)-3-buten-2-one, origin:Givaudan SA, Vernier, Switzerland¹²⁾4/3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde; origin:International Flavors & Fragrances, USA¹³⁾3-methyl-5-cyclopentadecen-1-one; origin: Firmenich SA, Geneva,Switzerland¹⁴⁾3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol;origin: Firmenich SA, Geneva, Switzerland¹⁵⁾(2Z)-2-phenyl-2-hexenitrile; origin: Firmenich SA, Geneva,Switzerland ¹⁶⁾2,4-dimethyl-3-cyclohexene-1-carbaldehyde; origin:Firmenich SA, Geneva, Switzerland ¹⁷⁾4-methyl-3-decen-5-ol; origin:Givaudan SA, Vernier, Switzerland

The addition of 700 parts by weight of 4-methyl-6-phenylhexan-2-ol tothe above-described composition imparted to the latter green andgardenia/lily of the valley connotation and boosted the violet of theoriginal composition.

What is claimed is:
 1. A method to confer, enhance, improve or modifythe odor properties of a perfuming composition, perfumed consumerproduct or perfumed article to impart lily of the valley/gardenia odornotes, the method comprising adding to said composition, product orarticle an effective amount of at least one compound of formula

in the form of any one of its stereoisomers or a mixture thereof andwherein one R represents a methyl group and the other R is a hydrogenatom, to impart the lily of the valley/gardenia odor notes.
 2. Themethod according to claim 1, wherein a compound of formula (I)represents 4-methyl-6-phenylhexan-2-ol.
 3. The method according to claim2, wherein a compound of formula (I) is(2RS,4RS)-4-methyl-6-phenylhexan-2-ol.
 4. The method according to claim3, wherein the compound is added to a perfuming composition thatincludes at least one ingredient selected from the group consisting of aperfumery carrier and a perfumery base; and optionally at least oneperfumery adjuvant.
 5. The method according to claim 2, wherein thecompound is added to a perfuming composition that includes at least oneingredient selected from the group consisting of a perfumery carrier anda perfumery base; and optionally at least one perfumery adjuvant.
 6. Themethod according to claim 2, wherein the perfumed article is a perfume,a fabric care product, a body-care product, an air care product or ahome care product.
 7. The method according to claim 3, wherein theperfumed article is a perfume, a fabric care product, a body-careproduct, an air care product or a home care product.
 8. The methodaccording to claim 1, wherein the compound is added to a perfumingcomposition that includes at least one ingredient selected from thegroup consisting of a perfumery carrier and a perfumery base; andoptionally at least one perfumery adjuvant.
 9. The method according toclaim 1, wherein the perfumed article is a perfume, a fabric careproduct, a body-care product, an air care product or a home careproduct.
 10. The method according to claim 1, wherein the perfumedconsumer product is a fine perfume, a cologne, an after-shave lotion, aliquid or solid detergent, a fabric softener, a fabric refresher, anironing water, a paper, a bleach, a shampoo, a coloring preparation, ahair spray, a vanishing cream, a deodorant or antiperspirant, a perfumedsoap, shower or bath mousse, oil or gel, a hygiene product, an airfreshener, a “ready to use” powdered air freshener, a wipe, a dishdetergent or hard-surface detergent.
 11. The method according to claim2, wherein the perfumed consumer product is a fine perfume, a cologne,an after-shave lotion, a liquid or solid detergent, a fabric softener, afabric refresher, an ironing water, a paper, a bleach, a shampoo, acoloring preparation, a hair spray, a vanishing cream, a deodorant orantiperspirant, a perfumed soap, shower or bath mousse, oil or gel, ahygiene product, an air freshener, a “ready to use” powdered airfreshener, a wipe, a dish detergent or hard-surface detergent.
 12. Themethod according to claim 3, wherein the perfumed consumer product is afine perfume, a cologne, an after-shave lotion, a liquid or soliddetergent, a fabric softener, a fabric refresher, an ironing water, apaper, a bleach, a shampoo, a coloring preparation, a hair spray, avanishing cream, a deodorant or antiperspirant, a perfumed soap, showeror bath mousse, oil or gel, a hygiene product, an air freshener, a“ready to use” powdered air freshener, a wipe, a dish detergent orhard-surface detergent.